A tandem synthesis of polypropionate chains. Highly stereoselective construction of the C(13)–C(25) segment containing nine contiguous chiral centers of swinholides A–C based on the stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminium

Abstract

The highly stereoselective synthesis of the common C(13)–C(25) segment containing nine contiguous chiral centers of swinholides A–C and misakinolide A has been achieved by tandem methodology which involves the stereospecific methylation of γ,δ-epoxy acrylates with trimethylaluminium and the novel reductive cleavage of an epoxy aldehyde with an organoselenium reagent as key steps.